HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Midway (MDW) to Caribbean from $106

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SJU
May 19 — May 261
From?
To?
Sun 5/19
Sun 5/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

How far in advance should I book a flight from Chicago Midway Airport to Caribbean?

Users have found that booking a flight from Chicago Midway Airport to Caribbean at least 57 days early can save you up to 20% on average compared to booking a flight this week. If booking 57 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Caribbean for as little as $258 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $280 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to Caribbean?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, October can be a great choice for travel to Caribbean. Flights to Caribbean from Chicago Midway Airport in October are about $318 on average during October, but can be found for as low as $90.

When is the cheapest time to fly from Chicago Midway Airport to Caribbean (MDW - CB)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Caribbean as you normally would.

Cheap Frontier flights from Midway to Caribbean

Explore cheap flight options specifically provided by Frontier for the route between Midway and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Tue 6/410:16 amMDW - SJU
1 stop16h 29mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/13$212
Tue 5/2810:52 amMDW - SJU
1 stop11h 49mFrontier
Sat 6/110:23 pmSJU - MDW
1 stop9h 31mFrontier
Deal found 5/13$213
Mon 9/1610:00 amMDW - SJU
1 stop10h 47mFrontier
Mon 9/2310:47 pmSJU - MDW
1 stop13h 08mFrontier
Deal found 5/13$214
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Wed 6/199:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/13$215
Thu 6/62:36 pmMDW - SJU
1 stop11h 32mFrontier
Wed 6/125:52 pmSJU - MDW
1 stop16h 39mFrontier
Deal found 5/13$216
Sun 6/92:26 pmMDW - SJU
1 stop11h 42mFrontier
Fri 6/148:41 pmSJU - MDW
1 stop12h 53mFrontier
Deal found 5/13$217
Tue 9/1710:00 amMDW - SJU
1 stop10h 47mFrontier
Sat 9/2110:18 pmSJU - MDW
1 stop13h 37mFrontier
Deal found 5/13$218
Mon 6/108:27 amMDW - SJU
1 stop17h 41mFrontier
Fri 6/1410:35 amSJU - MDW
1 stop14h 02mFrontier
Deal found 5/13$219
Mon 6/37:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 6/53:08 amSJU - MDW
1 stop7h 23mFrontier
Deal found 5/14$220

Cheap Delta flights from Midway to Caribbean

Explore cheap flight options specifically provided by Delta for the route between Midway and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Tue 6/46:00 amMDW - NAS
1 stop9h 29mDelta
Wed 6/55:49 pmNAS - MDW
1 stop15h 06mDelta
Deal found 5/13$351
Tue 6/46:00 amMDW - NAS
1 stop9h 29mDelta
Wed 6/55:49 pmNAS - MDW
2 stops24h 17mDelta
Deal found 5/13$356
Wed 9/1110:11 amMDW - SDQ
2 stops11h 29mDelta
Wed 9/182:56 pmSDQ - MDW
2 stops18h 49mDelta
Deal found 5/12$407
Wed 9/116:00 amMDW - SDQ
1 stop6h 23mDelta
Wed 9/182:56 pmSDQ - MDW
1 stop7h 48mDelta
Deal found 5/12$428
Wed 8/216:00 amMDW - NAS
1 stop6h 18mDelta
Wed 8/281:21 pmNAS - MDW
1 stop9h 26mDelta
Deal found 5/12$448
Sat 8/246:00 amMDW - MBJ
1 stop9h 05mDelta
Fri 8/302:25 pmMBJ - MDW
1 stop7h 22mDelta
Deal found 5/13$468
Sat 8/246:00 amMDW - MBJ
1 stop9h 05mDelta
Sat 8/312:25 pmMBJ - MDW
1 stop18h 47mDelta
Deal found 5/13$473
Wed 9/116:00 amMDW - STT
1 stop6h 14mDelta
Tue 9/172:24 pmSTT - MDW
1 stop8h 20mDelta
Deal found 5/12$478
Mon 6/36:00 amMDW - KIN
1 stop13h 56mDelta
Thu 6/69:00 amKIN - MDW
1 stop13h 01mDelta
Deal found 5/13$480

Cheap Midway to Caribbean flights in May & June 2024

Find cheap flight options from Midway to Caribbean specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Prices were last updated on May 14, 2024.
Wed 5/223:36 pmMDW - SJU
1 stop9h 13mFrontier
Wed 5/299:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/13$212
Tue 5/2810:52 amMDW - SJU
1 stop11h 49mFrontier
Sat 6/110:23 pmSJU - MDW
1 stop9h 31mFrontier
Deal found 5/13$213
Wed 5/293:04 pmMDW - SDQ
1 stop22h 45mFrontier
Tue 6/43:51 pmSDQ - MDW
1 stop22h 41mFrontier
Deal found 5/14$214
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Wed 6/199:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/13$215
Mon 6/37:23 pmMDW - PUJ
1 stop20h 33mFrontier
Tue 6/116:10 pmPUJ - MDW
1 stop14h 21mFrontier
Deal found 5/13$216
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 5/296:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/13$216
Sun 6/92:26 pmMDW - SJU
1 stop11h 42mFrontier
Fri 6/148:41 pmSJU - MDW
1 stop12h 53mFrontier
Deal found 5/13$217
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/13$218
Mon 6/108:27 amMDW - SJU
1 stop17h 41mFrontier
Fri 6/1410:35 amSJU - MDW
1 stop14h 02mFrontier
Deal found 5/13$219

Midway to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Midway and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Wed 5/223:36 pmMDW - SJU
1 stop9h 13mFrontier
Wed 5/299:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/13$212
Tue 5/2810:52 amMDW - SJU
1 stop11h 49mFrontier
Sat 6/110:23 pmSJU - MDW
1 stop9h 31mFrontier
Deal found 5/13$213
Wed 5/293:04 pmMDW - SDQ
1 stop22h 45mFrontier
Tue 6/43:51 pmSDQ - MDW
1 stop22h 41mFrontier
Deal found 5/14$214
Mon 9/1610:00 amMDW - SJU
1 stop10h 47mFrontier
Mon 9/2310:47 pmSJU - MDW
1 stop13h 08mFrontier
Deal found 5/13$214
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Wed 6/199:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/13$215
Mon 6/37:23 pmMDW - PUJ
1 stop20h 33mFrontier
Tue 6/116:10 pmPUJ - MDW
1 stop14h 21mFrontier
Deal found 5/13$216
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 5/296:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/13$216
Sun 6/92:26 pmMDW - SJU
1 stop11h 42mFrontier
Fri 6/148:41 pmSJU - MDW
1 stop12h 53mFrontier
Deal found 5/13$217
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/13$218

Midway to Caribbean flights leaving soon

Find last-minute flight options from Midway to Caribbean for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Wed 5/223:36 pmMDW - SJU
1 stop9h 13mFrontier
Wed 5/299:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/13$212
Tue 5/2810:52 amMDW - SJU
1 stop11h 49mFrontier
Sat 6/110:23 pmSJU - MDW
1 stop9h 31mFrontier
Deal found 5/13$213
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 5/296:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/13$216
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/13$218
Tue 5/2110:52 amMDW - SJU
1 stop11h 49mFrontier
Fri 5/319:29 amSJU - MDW
1 stop9h 58mFrontier
Deal found 5/13$223
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Mon 5/272:48 amSJU - MDW
1 stop29h 06mFrontier
Deal found 5/13$224
Wed 5/227:49 amMDW - SJU
1 stop8h 05mFrontier
Mon 6/38:59 amSJU - MDW
1 stop12h 02mFrontier
Deal found 5/13$226
Tue 5/2110:52 amMDW - SJU
1 stop11h 49mFrontier
Wed 5/2910:15 pmSJU - MDW
1 stop9h 39mFrontier
Deal found 5/13$227
Sat 5/182:35 pmMDW - SJU
1 stop8h 24mFrontier
Tue 5/212:51 pmSJU - MDW
1 stop7h 40mFrontier
Deal found 5/13$228

One-way flights to Caribbean from Midway

Search for one-way flight options from Midway to Caribbean. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Deal found 5/13$106
Wed 5/293:04 pmMDW - SDQ
1 stop22h 45mFrontier
Deal found 5/14$107
Mon 6/37:23 pmMDW - SJU
1 stop12h 21mFrontier
Deal found 5/13$107
Tue 6/117:36 pmMDW - NAS
1 stop14h 09mMultiple Airlines
Deal found 5/13$109
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Deal found 5/13$109
Tue 5/2810:52 amMDW - SJU
1 stop11h 49mFrontier
Deal found 5/13$110
Mon 6/108:27 amMDW - SJU
1 stop17h 41mFrontier
Deal found 5/13$113
Wed 5/227:49 amMDW - SJU
1 stop8h 05mFrontier
Deal found 5/14$114
Tue 8/2010:59 amMDW - SJU
1 stop12h 21mFrontier
Deal found 5/13$117

Find flights from Midway to Caribbean within your budget

Customize your flight search to find flights from Midway to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$212 - $640

Route

Depart

Return

Price

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 6/4

1 stop16h 29m

San Juan Luis Munoz Marin Intl

Tue 6/11

2 stops11h 20m

$212

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/28

1 stop11h 49m

San Juan Luis Munoz Marin Intl

Sat 6/1

1 stop9h 31m

$213

Chicago MidwaySanto Domingo Las Americas

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 5/29

1 stop22h 45m

Santo Domingo Las Americas

Tue 6/4

1 stop22h 41m

$214

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/16

1 stop10h 47m

San Juan Luis Munoz Marin Intl

Mon 9/23

1 stop13h 08m

$214

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 6/13

1 stop11h 32m

San Juan Luis Munoz Marin Intl

Wed 6/19

1 stop9h 24m

$215

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 6/3

1 stop20h 33m

Punta Cana

Tue 6/11

1 stop14h 21m

$216

Chicago MidwayNassau Intl

MDW - NAS

MDWNAS

Chicago Midway

Tue 6/4

1 stop9h 29m

Nassau Intl

Wed 6/5

1 stop15h 06m

$351

Chicago MidwayNassau Intl

MDW - NAS

MDWNAS

Chicago Midway

Wed 7/10

1 stop22h 57m

Nassau Intl

Tue 7/16

1 stop8h 03m

$367

Chicago MidwayKingston Norman Manley

MDW - KIN

MDWKIN

Chicago Midway

Thu 6/6

1 stop13h 56m

Kingston Norman Manley

Mon 6/17

1 stop12h 36m

$640

Flights are sorted by cheapest first

Deals found on 5/13

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated May 14, 2024.
Delta
8.0
Very good
10,706 reviews
Check prices

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,706 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

KLM
7.9
Good
1,569 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.5
Good
2,925 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,073 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Midway to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago Midway Airport to Caribbean for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Caribbean for under $300. The cheapest flight booked recently is on Frontier for just $212, but on average you can expect to pay $220.

  • Are there last-minute flights available from Chicago Midway Airport to Caribbean for under $300?

    There are currently 20+ open flights from Chicago Midway Airport to Caribbean within the next 7 days for less than $300.

  • What are the most popular routes from Chicago Midway Airport to Caribbean?

    The most popular flight routes from Chicago Midway Airport to Caribbean are Chicago Midway - San Juan Luis Munoz Marin Intl, Chicago Midway - Punta Cana and Chicago Midway - Montego Bay Sangster Intl.

  • What are the most popular airlines that fly from Chicago Midway Airport to Caribbean?

    When booking a flight from Chicago Midway Airport to Caribbean, you may want to consider flying on Delta, Frontier or Spirit Airlines as they are the most popular for this route.

  • What are the cheapest flights from Chicago Midway Airport to Caribbean?

    While on average a flight from Chicago Midway Airport to Caribbean is generally $162, our data shows the cheapest flight currently is $58. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $218 for that flight.

  • What does MDW to SJU mean?

    This is defined as Chicago Midway Airport (MDW) and San Juan Luis Munoz Marin Intl Airport (SJU). Codes like San Juan Luis Munoz Marin Intl Airport are often used to just call airports uniquely. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI).

  • Can I find deals for flights from Midway to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midway to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Caribbean.

  • Can I find deals for business class flights from Midway to Caribbean?

    Yes. Cheapflights offers flight deals from Midway to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Caribbean that allow pets onboard?

    Many airlines flying from Midway to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Caribbean?

    Yes, you can often find last-minute deals on Midway to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Caribbean flight deals updated?

    The Chicago Midway Airport to Caribbean flight deals you see on this page were last updated on 5/14.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Cancún flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Seattle flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Orlando flights
O'Hare Intl to Newark flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Boston flights
O'Hare Intl to Heathrow flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Athens flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
Midway to Newark flights
O'Hare Intl to Charles de Gaulle flights
O'Hare Intl to Denver flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Sky Harbor Intl flights
Midway to Cancún flights
Midway to Seattle flights
O'Hare Intl to Haneda flights
O'Hare Intl to Baltimore flights
O'Hare Intl to London City flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Dublin flights
O'Hare Intl to Gatwick flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Madrid flights
O'Hare Intl to San Diego flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Narita flights
O'Hare Intl to Nashville flights
Midway to Mexico City flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Frederic Chopin flights
O'Hare Intl to Istanbul flights
O'Hare Intl to Barcelona-El Prat flights
O'Hare Intl to Austin flights
Midway to LaGuardia flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Suvarnabhumi flights
O'Hare Intl to Dulles Intl flights
Midway to Hobby flights
Midway to Boston flights

Top 4 airlines flying from Midway to Caribbean

Discover the top 4 airlines that operate flights from Midway to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$350FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$165Average$267FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$361Average$732FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Alaska AirlinesCheapest$503Average$503FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
Denver to Phoenix flights
Dallas to Salt Lake City flights
Tampa to Miami flights
New York to Lisbon flights
Philadelphia to Chicago flights
Boston to Pittsburgh flights
New York to Las Vegas flights
Las Vegas to Denver flights
New York to Beijing flights
USA to Morocco flights
New Orleans to Houston flights
Chicago Midway Airport to Middle East flights

Search flights from Midway to Caribbean by cabin class

Find flights from Midway to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Midway to Caribbean

Find hourly flight availability from Midway to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 14, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Montes Claros
Flights to Girona Costa Brava
Flights to Naxos
Flights to Bourgas
Flights to Hyannis Barnstable
Flights to Samos
Flights to Reggio Calabria Tito Menniti
Flights to Devils Lake
Flights to Ningbo Lishe Intl
Flights to Pellston Emmet County
Flights to Provincetown
Flights to Cortez Montezuma County
Flights to Ohrid
Flights to Oran Es Senia
Flights to Menorca/Mahon
Flights to Hakodate
Flights to Ordu/Giresun
Flights to Laayoune Hassan I
Flights to Cornwall Newquay
Flights to Melilla
Flights to Rennes St Jacques
Flights to Parikia Paros
Flights to Constanţa Mihail Kogalniceanu
Flights to Miyakojima Hirara

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway to Caribbean?

Cheapflights makes it easy to find Midway to Caribbean flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Midway to Caribbean?

Millions of users choose and trust Cheapflights to book the best flight deals from Midway to Caribbean for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Midway to Caribbean with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway to Caribbean, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Midway to Caribbean become cheaper?

Of course! You can now track prices for flights from Midway to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines